Dinicotinic acid

Dinicotinic acid

Names
Preferred IUPAC name Pyridine-3,5-dicarboxylic acid
Other names 3,5-Pyridinedicarboxylic acid
Identifiers
CAS Number	499-81-0
3D model (JSmol)	Interactive image
Beilstein Reference	131640
ChEBI	CHEBI:46875
ChEMBL	ChEMBL446761
ChemSpider	9939
ECHA InfoCard	100.007.177
EC Number	207-893-8
Gmelin Reference	279307
PubChem CID	10366
UNII	N5NMH4PZ3D  Y
CompTox Dashboard (EPA)	DTXSID10198149
InChI InChI=1S/C7H5NO4/c9-6(10)4-1-5(7(11)12)3-8-2-4/h1-3H,(H,9,10)(H,11,12) Key: MPFLRYZEEAQMLQ-UHFFFAOYSA-N
SMILES C1=C(C=NC=C1C(=O)O)C(=O)O
Properties
Chemical formula	C7H5NO4
Molar mass	167.120 g·mol−1
Structure [1]
Crystal structure	monoclinic
Space group	P21/c, No. 14
Lattice constant	a = 9.702 Å, b = 11.153 Å, c = 6.587 Å α = 90°, β = 107.80°, γ = 90°
Formula units (Z)	4
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dinicotinic acid (pyridine-3,5-dicarboxylic acid) is a heterocyclic organic compound, more precisely a heteroaromatic. It is one of many pyridinedicarboxylic acids and consists of a pyridine ring carrying to carboxy groups in the 3- and 5-positions.

Preparation and properties

Dinicotinic acid can be formed by heating pyridine-2,3,5,6-tetracarboxylic acid or carbodinicotinic acid (pyridine-2,3,5-tricarboxylic acid). ^{[2] [3]}

The acid is sparingly soluble in water and ether. Its melting point of 323 °C is the highest among pyridinedicarboxylic acids. Upon heating, it decarboxylates and decomposes to nicotinic acid: ^[4]

References

1. Structure reports for 1973 : organic section. Organic compounds. J. Trotter. Dordrecht: Springer. 1975. p. 174. ISBN   978-94-017-3121-8. OCLC   859588799.
2. Meyer, Hans; Tropsch, Hans (1914). "Über Dinicotinsäure und deren Abbau zu ββ′-Diaminopyridin und über das αα′-Diaminopyridin". Monatshefte für Chemie (in German). 35 (2): 207–217. doi:10.1007/BF01518124. ISSN   0026-9247.
3. Wolffenstein, Richard (1922). Die Pflanzenalkaloide (in German) (Dritte, verbesserte und vermehrte Auflage ed.). Berlin, Heidelberg. p. 67. ISBN   978-3-642-92449-1. OCLC   913710178.
4. Alam, Mahbub; Khan, M. Hafeez (1980). "Preparation of some nicotinic acid derivatives". Philippine Journal of Science. 109 (1–2): 19–21.

See also

• Dipicolinic acid, an isomeric dicarboxylic acid